B7651

Brefeldin A

from Penicillium brefeldianum, ≥99% (HPLC and TLC), powder, activator of the sphingomyelin cycle

• Sinónimos: Nectrolide, γ,4-Dihydroxy-2-(6-hydroxy-1-heptenyl)-4-cyclopentanecrotonic acid λ-lactone, Ascotoxin, BFA, Cyanein, Decumbin
• Fórmula empírica (notación de Hill): C₁₆H₂₄O₄
• Número CAS: 20350-15-6
• Peso molecular: 280.36
• NACRES: NA.77
• PubChem Substance ID: 24278285
• UNSPSC Code: 12352200
• MDL number: MFCD12913297
• Beilstein/REAXYS Number: 25191
• Assay: ≥99% (HPLC and TLC)
• Form: powder

Propiedades

• Nombre del producto: Brefeldin A, from Penicillium brefeldianum, ≥99% (HPLC and TLC)
• biological source: Penicillium brefeldianum
• Quality Segment: 300
• assay: ≥99% (HPLC and TLC)
• form: powder
• solubility: DMSO: 10 mg/mL
• antibiotic activity spectrum: neoplastics
• mode of action: protein synthesis | interferes
• storage temp.: 2-8°C
• SMILES string: C[C@H]1CCC\C=C\[C@@H]2C[C@H](O)C[C@H]2[C@H](O)\C=C\C(=O)O1
• InChI: 1S/C16H24O4/c1-11-5-3-2-4-6-12-9-13(17)10-14(12)15(18)7-8-16(19)20-11/h4,6-8,11-15,17-18H,2-3,5,9-10H2,1H3/b6-4+,8-7+/t11-,12+,13-,14+,15+/m0/s1
• InChI key: KQNZDYYTLMIZCT-KQPMLPITSA-N

Descripción

General description

Brefeldin A (BFA) is a fungal metabolite containing a 13-membered macrocyclic lactone ring. [1] It inhibits protein and nucleic acid synthesis. BFA blocks the exchange of GDP for GTP on adenosine ribosylation factors (ARFs), thereby hindering the binding of coat protein (β-COP) and consequently disrupts the structure and function of the Golgi apparatus. BFA is an activator of the sphingomyelin cycle. Brefeldin A-mediated apoptosis has been observed in human tumor cells. Brefeldin A has been shown to increase CRISPR-mediated homology-directed repair (HDR) efficiency. It demonstrates a diverse array of biological functions, including antitumor, antiviral, antibiotic, antimitotic, antifungal and antinematodal properties.

Application

Brefeldin A has been used to:

• increase CRISPR genome editing efficiency.
• facilitate the measurement of cytokine production[2]
• block intracellular transports in cell culture experiments[1]

Biochem/physiol Actions

Brefeldin A (BFA) is a fungal metabolite which disrupts the structure and function of the Golgi apparatus. BFA is an activator of the sphingomyelin cycle. Brefeldin A-mediated apoptosis has been observed in human tumor cells.

Brefeldin A has been shown to increase CRISPR-mediated homology-directed repair (HDR) efficiency.

Disrupts the structure and function of the Golgi apparatus; activator of the sphingomyelin cycle.

Información de seguridad

• pictograms: GHS06
• signalword: Danger
• hcodes: H301
• pcodes: P301 + P310
• Hazard Classifications: Acute Tox. 3 Oral
• Clase de almacenamiento: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves